First Biosynthetic pathway of 1-hepten-3-one in Iporangaia pustulosa (Opiliones)

Author(s)

Rocha, Daniele F. O. ^[1] ; Wouters, Felipe C. ^[1] ; Machado, Glauco ^[2] ; Marsaioli, Anita J. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Univ Sao Paulo, Inst Biociencias, Dept Ecol, BR-05508090 Sao Paulo - Brazil

• Document type: Journal article
• Source: SCIENTIFIC REPORTS; v. 3, NOV 6 2013.
• Web of Science Citations: 5

Abstract

Arthropods produce a great variety of natural compounds, many of which have unexplored biosynthesis. Among the armored harvestmen (Arachnida: Opiliones) of the suborder Laniatores, the defensive gland exudates contain vinyl ketones and other constituents of supposed polyketide origin. We have studied the biosynthesis of 1-hepten-3-one in the Neotropical harvestman Iporangaia pustulosa by feeding individuals with C-13-labeled precursors, demonstrating its mixed acetate/propionate origin. C-13 NMR spectroscopy showed an unusual labeling pattern suggesting different propionate sources for starting and extender units. Our analysis also indicates the presence of methylmalonyl-CoA mutase, converting acetate into propionyl-CoA via succinyl-CoA, together with other C-3 unit routes. This is the first biosynthetic study of alkyl vinyl ketones in arthropods. Our results shed light on the origin and diversification of chemical compounds in a major arthropod group. (AU)

• FAPESP's process: 08/06604-7 - Cladistics of the harvestmen of the family Gonyleptidae (Arachnida: Opiliones) based on morphological, behavioral and molecular characters
• Grantee: Ricardo Pinto da Rocha
• Support Opportunities: Regular Research Grants